Small-Group Chianti and San Gimignano Sunset Trip from Siena

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Summary
Experience Details
What You’ll Experience
Where to Meet
Reviews
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Duration
8 hours
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Number of Guests
1 - 9 guests
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Language
English
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Digital Ticket
Mobile or paper ticket accepted

Discover Chianti's lush landscapes and renowned wines on this small-group tour from Siena. Explore San Gimignano's medieval charm and savor a farm-to-table dinner as the sun sets over Tuscany.

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For each guest that attends this experience, byFood will donate
10 meals

Experience Details

On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak forests and cypress trees – and discover its famous wine by visiting a local producer, touring their cellars and tasting their wines. Then head to the UNESCO World Heritage town of San Gimignano, famous for its medieval towers. Enjoy the main sights and browse the streets and boutique stores just as the day's crowds begin to dwindle. Visit a local farm and enjoy a farm-to-table dinner of its products and wines during sunset, in a stunning location overlooking the San Gimignano towers and the rolling, vine-covered hills.

What You Get

Traditional dinner at farm
Professional Guide
Transport by air-conditioned minivan
Gratuities
Hotel pickup and drop-off
Entrance fees to attractions in San Gimignano

Good To Know

  • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
  • Not recommended for travelers with poor cardiovascular health
  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Specialized infant seats are available

What You’ll Experience

Basilica Cateriniana Di S. Domenico (Pass By)

Meet your tour guide at 2.30pm in front of the church of San Domenico in Siena and begin the tour with a comfortable drive through the Chianti countryside. Visit a Chianti wine estate, where you'll tour the grounds and wine cellars while learning about the wine-making process. Sit down and savor a tasting of Black Rooster Chianti Classico wine.
1

Cantinetta di Monteriggioni

After visiting a Chianti winery, visit a historic town that was once of fortress, Monteriggioni, to marvel at the medieval towers that are still intact. Monteriggioni is a perfectly preserved medieval town with a complete ring of walls and turrets, once Siena’s main bastion of defense against the armies of Florence. Today it is a quiet hamlet and you can enjoy leisure time exploring the charming streets and stores of local crafts.
30 minutesAdmission Ticket Free
2

Historic Centre of San Gimignano

In the late afternoon, arrive in San Gimignano as the crowds begin to dwindle and the many streets and squares of this medieval town of towers that flourished thanks to the via Francigena, an important trade route. Enjoy free time to enter its impressive church, the Collegiata di San Gimignano, or to explore the Civic Museum (entrance fees at own expense). Alternatively, shop the artisan boutiques for leather goods and hand-painted pottery; sample the fruits of the soil in the food shops and wine bars or discover the town’s many hidden beauties.
1 hourAdmission Ticket Free
3

Strada Statale 222 Chiantigiana

After your time in San Gimignano, head out of town to a nearby rustic farmhouse, where you'll be treated to a classic Tuscan dinner accompanied by wine. Enjoy the farm's products and wine over a convivial dinner with the others on tour that you can now call new friends.
2 hoursAdmission Ticket Included

Meeting & Pickup

Meeting Point

Piazza San Domenico, Siena Provincia di Siena Toscana, Italy, IT, 53100

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Meet under the large tree next to the red brick church
End Point

This experience ends at the meeting point.

Cancellation Policy

Cancel your booking at least 24 hours before the experience start time to receive a full refund minus a 3.2% transaction fee.

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What People Are Saying
Overall ratings and reviews
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(60)
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Well worth the experience!
July 31, 2025
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(TripAdvisor)

The tour was impeccable from beginning to end. Organised and professional. Our tour leader, Georgia, was knowledgeable, friendly, fun and accomodating. Highly recommend this tour to get a taste of ...read more

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Amazing Tuscan Experience - MUST DO!!
July 02, 2025
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(TripAdvisor)

Oh my gosh! Where do I even begin?! This is EVERYTHING I wanted in a Tuscan wine tour! Gorgeous little stops at San Gimignano and Monteriggoni. A gorgeous Chianti winery tour and a beautiful Tuscan...read more

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..
June 01, 2025
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(TripAdvisor)

Perfect small towns , chianti region , wine degustation , excellent tour guide . Miniven … not very comfortabl/ seats so so /.

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Great wine, delicious food and beautiful views of Tuscany from San Gimignano and Monteriggioni
May 06, 2025
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(TripAdvisor)

We spent a delightful tour with Kiko who is an incredible tour guide. We visited two beautiful vineyards, had a delicious dinner at a family owned farm, as well as a stop in two special cities alon...read more

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Wine tour with personality
April 27, 2025
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(Viator)

This experience was intimate, informative and full of fun, bumpy roads and all. The afternoon/evening flew by very quickly!

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from  $187.30 
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Please note that the time is in Central European Time.
Free cancellation (24 hours notice)
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Earliest available date: August 20, 2025
from  $187.30  per guest
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Please note that the time is in Central European Time.
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals
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